134807-23-1Relevant articles and documents
Synthesis and regioselective hydrolysis of 2-imidazol-1-ylsuccinic esters
Zaderenko,Gil,Ballesteros,Cerdan
, p. 6268 - 6273 (1994)
(±)-2-Imidazol-1-ylsuccinic esters were synthesized by thermal addition of imidazole to either fumaric or maleic esters. Acceleration of the reaction was achieved, in some cases, using microwave heating. These esters underwent an easy regioselective hydrolysis, under neutral conditions, to give the corresponding half-esters: (±)-3-(alkoxycarbonyl)-2-imidazol-1-ylpropionic acids, through either BAC3 or BAL1 mechanisms. Kinetic studies in H2O and D2O as well as 18O and 17O labeling experiments supported the proposed mechanism. The results of these hydrolyses, which depended on the nature of the alcohol moiety, were compared with those obtained with some imidazol-1-ylacetate analogues or with (±)-2-pyrazol-1-yl- and benzimidazol-1-ylsuccinic esters. In general, imidazolylsuccinic esters hydrolyzed faster than the homologous derivatives from pyrazole or benzimidazole.
RETROVIRAL PROTEASE INHIBITING COMPOUNDS
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, (2008/06/13)
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